Stoney Gillespie Jr. is a premium cigar enthusiast with 20 years of experience in event organization. Additionally, he has had the opportunity to travel to various countries in search of knowledge, learning about the immaculate purity of tobacco, the soils, and the inherent beauty of cigars.
Over the years, he has attended various events in the United States, including some of the industry’s first events, which sparked a new wave and provided opportunities to showcase the cigar cultures of different cities, highlight smaller boutique cigar brands, and tobacco-related businesses.
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Driven by these experiences, Stoney became a co-founder of The Chicago Cigar Week, an initiative created to introduce cigar enthusiasts from around the world to the cigar culture in his city.
To achieve this, the event includes several activities at different locations throughout the Chicagoland area, allowing visitors to participate and experience the Windy City’s lifestyle.
Some of their standout events include golf games, wine and whiskey pairings, coffee and tea pairings, as well as educational panels organized by the SOTL Global Movement, and events sponsored by leading manufacturers, brand owners, and industry cigar enthusiasts.
The Chicago Cigar Week has also featured a brunch on a cruise across Lake Michigan, where guests enjoyed a panoramic view of the Chicago skyline accompanied by a fine cigar.
The effort to promote local culture has also led to events at the historic South Shore Cultural Center and the Drake Hotel, as well as exclusive venues such as the Fairplay Compass Arena, Pinstripes Rooftop, Park Tavern, Pier 31 on Lakeshore, Veterans Memorial Park, home to the Chairman Fred Hampton Aquatic Center, and the 63rd Beach House Promenade and Courtyard Fountain, not to mention the numerous lounges, essential sites in Chicago’s tobacco culture.
According to Stoney, the first Chicago Cigar Week took place in July 2022, and it recently celebrated its third annual event, “and we’ve already started planning the fourth edition, which will be held from July 23 to 27, 2025.”
Chicago, unlike many other cities, faces unique challenges regarding tobacco restrictions. However, supported by extensive event planning experience, Stoney and the other organizers have been able to overcome these by incorporating creativity into their planning, using private event venues and various locations that create conducive atmospheres for smokers.
Regarding the SOTL Global Movement, Stoney believes that the tobacco scene in Chicago has seen tremendous growth in favor of women, with more female lounge or cigar-related business owners. “Their knowledge and experience in the cigar industry are invaluable!”
But the industry’s growth is not limited to women alone, as The Chicago Cigar Week also reports an increase in attendance, with more national visitors from New York, New Jersey, Philadelphia, California, Georgia, Tennessee, Kentucky, Louisiana, Mississippi, Alabama, Nevada, North and South Carolina, Oklahoma, Indiana, Wisconsin, Ohio, Arkansas, Texas, Miami, St. Louis, and Detroit, as well as international visitors from countries such as Canada, Mexico, the Dominican Republic, and Nicaragua.
